The question was, “If you could have dinner with anyone, who would it be?” My answer: Chris Brown.

During a magazine interview last year, I was asked a series of get-to-know-you questions. What books are you reading? Where do you like to vacation? What’s your passion? But my answer to the dinner question prompted a puzzled looked from the interviewer. I’m a journalist, so one might assume I’d say I’d like to have dinner with a world leader, or a famed journalist, or maybe a historical figure.

Clearly, I’m not in Chris Brown’s core fan base. I’m not a teenage girl. And though I like some of his music, I’ve never been more than a casual fan. After his brutal assault on his then-girlfriend Rihanna in 2009, I was done with him. I was disgusted by him and his abusive behavior. I went so far as removing his songs from my iPod because I wasn’t comfortable with even that tacit support of a man who would hit a woman.

Brown hasn’t done much in the past few years to gain sympathy. After pleading guilty to felony assault and being sentenced to probation for the Rihanna incident, he faces another assault charge for allegedly punching a man in Washington, D.C., late last year, and he now sits in jail after being kicked out of court-ordered rehab for “failure to comply with the rules and regulations of the program.”

This is the second time he’s been booted from a rehab facility. Throw in the Drake and Frank Ocean incidents, the broken window at “Good Morning America,” his rants and feuds on Twitter, and his overall unapologetic, arrogant, sometimes vulgar demeanor, and it would be pretty easy to write him off as a young, privileged, immature punk who hasn’t learned his lesson, thinks he’s above the law and isn’t deserving of our sympathy or support.

Brown has a formidable core of rabid fans who will support his career no matter what he does in his personal life. Other Brown fans are able to separate his art from his personal dealings. In other words, liking his music doesn’t mean endorsing him on a personal level. And, for others, there’s still something unsettling about enthusiastically embracing the art of someone who behaves so badly. That’s the category I was in for years.

When it comes to celebrities, our support is more often focused on their professional endeavors. Buying a person’s music, going to see a star’s movies, buying an athlete’s jersey, etc., are examples of how we support them. Brown still enjoyed huge commercial success, and his only Grammy award came after he pleaded guilty to assaulting Rihanna. She forgave him. The public seemingly forgave him. His career rebounded. His life, though? That’s another story.

He’s only 24 years old. I refuse to believe Brown’s only contributions to this world will be singing, dancing and mayhem. If Twitter is any measure of influence, with 13 million followers, he has influence. He’s the fourth most popular black man in the world on Twitter behind President Obama, Lil Wayne and Drake. (Felt weird writing those names in the same sentence.)

Bottom line: I hate to see a young black man fail on such an epic and public scale. I find Brown to be somewhat emblematic. There are countless troubled young Black men about whom you’ll never hear, who have people giving up on them every single day. Of course, Brown has had success and many advantages that most young men can only imagine. Yet, he’s not immune to the same issues with family, violence and the legal system that confront many young men who don’t have his fans or resources.

If only all young Black men had a core fan base in this country like Brown’s that would stick with them and see their talent and potential even as they struggle. But should Chris Brown be excluded from our moral and emotional support, the same type many young Black men need, just because he happens to be rich and famous?

No, Brown didn’t have it easy as a child. Most don’t. He’s described growing up poor, but it was a childhood that, according to Brown, also included domestic violence and “losing his virginity” at the age of 8. That childhood has obviously had an impact on his difficult transition to adulthood. But even if you want to sympathize, Brown has done little to come across as a sympathetic figure.

At some point, he has to take responsibility for his own life, commit to improving himself and pay his debt to society. Then the public will decide whether to support his music career. But his youth, his story, his talent and his influence could all potentially shape the kind of successful life that can’t be measured by record sales. Or he may end up another cautionary tale.

One of his probation reports states: “He remains thankful to the court for the opportunity to find out and learn more about himself, his anger issues and the type of person he wants to become, which is a man who is able to better himself and be a positive role model.”

I can only hope that’s true and would love to hear more about his plans over dinner … because at this point, if we’re handing out second chances, Brown hasn’t exactly earned a spot at the front of the line.

(T.J. Holmes is a journalist and TV personality. Formerly of CNN, he can currently be found at MSNBC, and his commentary can be found online. Follow him on Twitter.)